6-Bromo-8-chloro-7-isopropoxy-2,2-dimethyl-chroman-4-one → 6-Bromo-8-chloro-7-isopropoxy-4-isopropyl-2,2-dimethyl-2H-chromene

HRID 2180470Notes

Reaction equation

HRID 2180470 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([Cl:21])[C:16]=1[O:17][CH:18]([CH3:20])[CH3:19])[O:13][C:12]([CH3:23])([CH3:22])[CH2:11][C:10]2=O>C1COCC1>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([Cl:21])[C:16]=1[O:17][CH:18]([CH3:20])[CH3:19])[O:13][C:12]([CH3:23])([CH3:22])[CH:11]=[C:10]2[CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 224907866-Bromo-8-chloro-7-isopropoxy-2,2-dimethyl-chroman-4-one2×HCID 178418918HCID 178418918, compound

Product 1

HCID 224909526-Bromo-8-chloro-7-isopropoxy-4-isopropyl-2,2-dimethyl-2H-chromene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure C, isopropylmagnesium chloride (2.0 M in THF, 18.8 mL, 37.6 mmol), 6-bromo-8-chloro-7-isopropoxy-2,2-dimethyl-chroman-4-one, (Compound 11, 2.6 g, 7.5 mmol) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(]-pyrimidinone (DMPU, 4.5 mL, 37.6 mmol) in THF was reacted to afford the title compound as a yellow oil after purification by flash chromatography (silica gel, 5% to 10% ethyl acetate in hexanes).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-7bece486e3ab4a8b97081fb1b4617bdc
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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